HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$104+ Cheap flights from Vermont to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Aug 8 — Aug 151
Sat 8/8
Sat 8/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Vermont to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Vermont to Chicago

Cheapest flights from Vermont to Chicago
Explore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:15 pm
BTV
-
ORD
1 stop20h 17m
Multiple Airlines
Tue 10/207:00 am
ORD
-
BTV
1 stop8h 35m
Multiple Airlines
Deal found 7/8$267
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:00 am
BTV
-
ORD
Nonstop2h 44m
United Airlines
Sun 8/26:15 pm
ORD
-
BTV
Nonstop2h 19m
United Airlines
Deal found 7/8$269
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:30 am
BTV
-
ORD
Nonstop2h 52m
American Airlines
Wed 8/127:04 pm
ORD
-
BTV
Nonstop2h 24m
American Airlines
Deal found 7/7$270
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:30 am
BTV
-
ORD
Nonstop2h 52m
American Airlines
Fri 8/143:40 pm
ORD
-
BTV
Nonstop2h 23m
American Airlines
Deal found 7/8$275
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:30 pm
ALB
-
ORD
1 stop5h 00m
American Airlines
Fri 8/146:45 am
ORD
-
ALB
1 stop6h 59m
American Airlines
Deal found 7/8$287
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:20 pm
ALB
-
ORD
Nonstop2h 36m
United Airlines
Tue 8/412:08 pm
ORD
-
ALB
Nonstop2h 09m
United Airlines
Deal found 7/8$288
This KAYAK deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:15 am
ALB
-
MDW
1 stop6h 36m
Delta
Thu 8/65:10 pm
MDW
-
ALB
1 stop5h 47m
Delta
Deal found 7/8$288
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:13 pm
ALB
-
ORD
Nonstop2h 47m
American Airlines
Sun 8/96:45 am
ORD
-
ALB
1 stop6h 59m
American Airlines
Deal found 7/8$289
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:20 pm
ALB
-
MDW
Nonstop2h 05m
Southwest
Sun 9/135:00 am
MDW
-
ALB
1 stop4h 20m
Southwest
Deal found 7/8$289
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:50 am
BTV
-
MDW
1 stop5h 49m
Delta
Wed 11/116:30 pm
MDW
-
BTV
1 stop3h 37m
Delta
Deal found 7/8$289
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:15 am
BTV
-
ORD
1 stop6h 53m
Delta
Sat 8/293:25 pm
ORD
-
BTV
1 stop6h 06m
Delta
Deal found 7/8$289
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:58 pm
ALB
-
ORD
1 stop5h 59m
Delta
Mon 8/1011:23 am
ORD
-
ALB
2 stops10h 54m
Delta
Deal found 7/8$292

Find flight deals from Vermont to Chicago

Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated July 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(Kiwi.com)

One-way from

$104
(United Airlines)

Popular in

January

Cheapest in

May

Average price

$324

Good round-trip deal

$376 or less

Good one-way deal

$304 or less
Provider with most accurate pricing for Burlington-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Burlington-Chicago (CHI) flights.
Search Deals
From Vermont to Chicago (CHI)
Search Deals
One-way flight from Vermont to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Vermont to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Vermont to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vermont to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 9, 2026.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 9/19

4:47 pm-6:31 pm

Nonstop2h 44m

Chicago O'Hare Intl

Mon 9/21

6:15 pm-9:38 pm

Nonstop2h 23m

$269

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 8/29

6:00 am-7:39 am

Nonstop2h 39m

Chicago O'Hare Intl

Sun 8/30

7:30 am-11:03 am

Nonstop2h 33m

$269

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 10/7

6:00 am-11:48 am

1 stop6h 48m

Chicago O'Hare Intl

Sat 10/10

7:25 am-10:47 am

Nonstop2h 22m

$279

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Thu 8/20

3:38 pm-5:29 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sun 8/23

6:00 am-2:23 pm

1 stop7h 23m

$288

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 11/7

11:50 am-4:39 pm

1 stop5h 49m

Chicago Midway

Wed 11/11

6:30 pm-11:07 pm

1 stop3h 37m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 8/28

7:15 am-12:39 pm

1 stop6h 24m

Chicago Midway

Mon 8/31

5:45 pm-11:21 pm

1 stop4h 36m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 9/19

7:30 am-12:39 pm

1 stop6h 09m

Chicago Midway

Wed 9/23

5:11 pm-11:58 pm

1 stop5h 47m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 8/22

1:15 pm-6:33 pm

1 stop6h 18m

Chicago Midway

Fri 8/28

6:42 pm-11:21 pm

1 stop3h 39m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 9/19

7:30 am-12:39 pm

1 stop6h 09m

Chicago Midway

Tue 9/22

5:11 pm-11:58 pm

1 stop5h 47m

$289

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 8/29

1:15 pm-4:17 pm

1 stop4h 02m

Chicago O'Hare Intl

Mon 8/31

5:20 pm-11:21 pm

1 stop5h 01m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Vermont to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Vermont with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Vermont to Chicago

What is the cheapest month to book a flight from Vermont to Chicago?

Currently, November is the cheapest month in which you can book a flight from Vermont to Chicago (average of $99). Flying from Vermont to Chicago in January is currently the most expensive (average of $209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from VT to CHI?

Find hourly flight availability from Vermont to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 9, 2026.

One of the essential ways to save on airfare from Vermont to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 76% on airfare.

Weekly flight availability from Vermont to Chicago

Explore weekly flight availability from Vermont to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 9, 2026.

The most flights from USVT to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Vermont to Chicago?

How far ahead should I book a flight from Vermont to Chicago?

Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vermont to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

Find useful and relevant information for your journey from Vermont to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Vermont to Chicago?

    Departing from Vermont to Chicago will take you 2h 44m. The distance between Vermont and Chicago is about 761 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Vermont to Chicago?

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Albany Intl - Chicago O'Hare Intl or Hartford Bradley Intl - Chicago Midway when deciding on the best route from Vermont to Chicago.

  • What are the most reliable airlines from Vermont to Chicago?

    No one likes to see their flight delayed. When booking a flight from Vermont to Chicago consider choosing United Airlines (78%), Air New Zealand (78%) or Qatar Airways (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Vermont to Chicago?

    Looking at all options, your cheapest flight can be booked for $217. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $212 on average, our data indicates $867 when flying from Vermont to Chicago.

  • Can I find deals for flights from Vermont to Chicago that include hotel bookings?

    Yes. In addition to deals on Vermont to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vermont to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vermont to Chicago.

  • Can I find deals for business class flights from Vermont to Chicago?

    Yes. Cheapflights offers flight deals from Vermont to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Vermont to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Vermont to Chicago (average of $99). Flying from Vermont to Chicago in January is currently the most expensive (average of $209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Vermont to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Seattle to O'Hare Intl flights
Hobby to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Newark to Midway flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
Boston to O'Hare Intl flights
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
LaGuardia to Midway flights
Raleigh to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Baltimore to Midway flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to Midway flights
Dulles Intl to Midway flights
Miami to O'Hare Intl flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
John F Kennedy Intl to Midway flights
San Francisco to Midway flights
Atlanta to Midway flights
San Diego to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hobby to Midway flights
Minneapolis to O'Hare Intl flights
Seattle to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
Philadelphia to Midway flights
Portland to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Tampa to Midway flights
Cleveland to O'Hare Intl flights
New Orleans to O'Hare Intl flights
Denver to Midway flights

Top 2 airlines flying from Vermont to Chicago

Discover the top 2 airlines that operate flights from Vermont to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$323FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$366FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.